Sailing Trips in Hawaii
Top 10 Best Hawaii Sailing Trips
Found 104 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE in the US! Join us for a beautiful Hawaiian sunset!! We have been sailing the Pacific waters off of the Island of Oahu since 1985... More
Oahu Catamaran Waikiki Sunset on 40 Foot Catamaran: Food and BYOB
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Hawaii
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Superb994 reviews4.9
2025 VIATOR TOP 10 award for WATER EXPERIENCES in the UNITED STATES including the TOP SUNSET CRUISE ....
Kauai’s Na Pali Coast Snorkel and Sail Tour
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour catamaran journey combines spectacular sightseeing, exciting snorkeling, and all-inclusive comfort, making it the top choice for fami... More
Kauai’s Na Pali Coast Snorkel and Sail Tour
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Hawaii
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Superb572 reviews4.8
Set sail for a once-in-a-lifetime adventure along Kauai’s iconic Na Pali Coast. This five-hour cat....
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adventure, relaxation, and a beautiful Hawaiian sunset in one unforgettable trip. Start your adventure at Turtle Canyon, where you c... More
Waikiki Turtle Snorkeling Tour 6 Activities + & Sunset Cruise
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Hawaii
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Superb39 reviews5
Our Sunset Turtle Snorkeling Tour offers a unique all-in-one Waikiki ocean experience, combining adv....
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury sailing catamaran? Perfect for families, couples, kids, first-time snorkelers, and ocean lovers, this Lahaina adventure combines a... More
Lahaina Maui Sea Turtle Snorkel Sail Adventure w/Lunch & Open Bar
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Hawaii
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Superb120 reviews4.9
Ready for an unforgettable day of sailing, snorkeling, island lunch, and open bar aboard our luxury ....
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More
Four Winds Molokini Snorkeling Tour from Maalaea Harbor
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Hawaii
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Superb854 reviews4.7
Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....
Paragon Lahaina Sunset Sail
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from Lahaina Harbor. Enjoy the afternoon hours at sea in the glassy, miraculous ‘au’au Channel is like floating inside an infinite ... More
Paragon Lahaina Sunset Sail
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Hawaii
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Superb28 reviews4.9
Join us aboard our flagship sailing catamaran, Paragon, for an unforgettable Maui sunset sail from L....
Waikoloa Signature Catamaran Sunset Sail
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. Departing from Anaeho‘omalu Bay, the Spirit of Aloha catamaran offers a smooth, comfortable ride with panoramic views of Mauna Kea... More
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Waikoloa Signature Catamaran Sunset Sail
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Hawaii
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Superb415 reviews4.7
End your day in paradise with a relaxing sunset cruise along Waikoloa’s beautiful Kohala Coast. De....
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Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, socialize with friends and family and take in the spectacular Maui sunset.... More
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Maui Catamaran Sunset Cocktail Cruise from Ma'alaea Harbor
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Hawaii
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Exellent24 reviews4.5
Join us aboard the Malolo for drinks as we cruise gently along the Maui coastline. Sit back, relax, ....
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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui sunset begin to paint the sky. As you step aboard, you're greeted by the friendly crew who welcome you with warm aloha spirit. The c... More
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Luxury Catamaran Royal Sunset Dinner Sail (Adults-Only)
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Hawaii
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Superb60 reviews4.8
Picture yourself boarding Alii's newest and most elegant catamaran as the golden hues of the Maui su....
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Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-built for the Hilton Hawaiian Village Waikiki Beach Resort. See the island like never before as you set sail from the only pier in W... More
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Waikiki Sunset Cocktail Cruise - Hilton Hawaiian Village
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Hawaii
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Exellent37 reviews4.5
Explore the Waikiki coastline aboard the new Spirit of Aloha, a 65-foot sailing catamaran custom-bui....
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Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest luxury custom built catamarans and includes breakfast, lunch, dessert and an open bar. This is our award-winning snorkel tour that... More
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Maui: 5-hour Snorkel w/ BBQ Lunch & Open Bar from Kaanapali
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Hawaii
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Superb31 reviews4.9
5-hour, two-spot snorkel is unlike any other on Ka'anapali Beach as it's aboard Ka'anapali's newest ....
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Day's End Cocktail Sunset Sail
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most scenic cocktail hour. Happy hour at sea with handcrafted drinks, vibrant music, and a relaxed-yet-refined vibe that turns every pour ... More
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Day's End Cocktail Sunset Sail
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Hawaii
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Superb95 reviews4.7
Drift away aboard our 65’ luxury sailing catamaran and sail into golden hour for Maui’s most sce....
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Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki coastline and snorkel at Turtle Canyon. Our eco-conscious cruise lets you see whales (December through March), fish, even green s... More
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Hilton Hawaiian Village Turtle Snorkel with Optional Lunch
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Hawaii
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Exellent47 reviews4.3
Swim with turtles and fish, while enjoying the crystal blue topical waters. Sail the scenic Waikiki....
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Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More
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Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea
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Hawaii
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Superb316 reviews4.8
Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....
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Deluxe Sail & Snorkel to the Captain Cook Monument
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters a... More
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Deluxe Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb576 reviews4.9
Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient la....
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Half-Day Deluxe Molokini Snorkel Excursion in Maui
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More
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Half-Day Deluxe Molokini Snorkel Excursion in Maui
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Hawaii
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Superb130 reviews4.9
Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....
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Snorkel with Manta Rays Guaranteed
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More
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Snorkel with Manta Rays Guaranteed
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Hawaii
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Superb757 reviews4.8
Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....
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Waikiki Sunset Cruise from Oahu
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks and a submerged glass-bottom viewing room, you’ll have an ideal vantage point to observe marine life such as dolphins, whales, sea... More
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Waikiki Sunset Cruise from Oahu
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Hawaii
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Superb71 reviews4.7
Experience a Hawaiian sunset sail aboard our 55-foot double-decker catamaran. With spacious decks an....
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Afternoon Sail & Snorkel to the Captain Cook Monument
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More
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Afternoon Sail & Snorkel to the Captain Cook Monument
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Hawaii
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Superb740 reviews4.9
A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....
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Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More
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Best Waikiki Sunset Cruise: BYOB Sunset Sail with Swimming
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Hawaii
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Superb210 reviews4.9
Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....
Free Cancellation
(Saving inf% )